Water → HCID 15056158, compound

HRID 1650853Notes

Reaction equation

HRID 1650853 reaction equation
[Si]([O:8][C@H:9]1[CH2:13][N:12]([C:14]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=2)=[O:15])[C@H:11]([CH2:27][NH:28][C:29](=[O:33])[CH:30](Cl)[CH3:31])[CH2:10]1)(C(C)(C)C)(C)C.[O-:34][C:35]#[N:36].[K+].O>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C)C=O>[OH:8][C@H:9]1[CH2:13][N:12]([C:14]([O:16][CH2:17][C:18]2[CH:19]=[CH:20][C:21]([N+:24]([O-:26])=[O:25])=[CH:22][CH:23]=2)=[O:15])[C@H:11]([CH2:27][N:28]2[C:29](=[O:33])[CH:30]([CH3:31])[NH:36][C:35]2=[O:34])[CH2:10]1

Participants

6

Reactant 3

HCID 962WaterHCID 11378442Potassium cyanateHCID 56996121HCID 56996121, compound

Product 1

HCID 15056158HCID 15056158, compoundYield 56.5%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of (2S,4R)-4-(t-butyldimethylsilyloxy)-2-(2-chloropropionyl)aminomethyl-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (18.4 g), potassium cyanate (14.9 g) and tetrabutylammonium iodide (13.6 g) in N,N-dimethylformamide (180 ml) was stirred at 100°-110° C. for 3 hours. The reaction mixture was poured into water (300 ml) and extracted twice with ethyl acetate (200 ml). The extract was washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and evaporated in vacuo. The resulting residue was dissolved in a mixture of methanol (150 ml) and concentrated hydrochloric acid (6.1 ml). The solution was stirred at ambient temperature for 2 hours and evaporated in vacuo. The resulting residue was chromatographed on silica gel (250 g) eluting with a mixture of chloroform and methanol (19:1, V/V). The fractions containing the desired compound were collected and evaporated in vacuo to give (2S,4R)-4-hydroxy-2-(4-methyl-2,5-dioxoimidazolidin-1-yl)methyl-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (8.16 g).

Workup

  1. extractionextracted twice with ethyl acetate (200 ml)
  2. washThe extract was washed with saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated in vacuo
  5. dissolutionThe resulting residue was dissolved in a mixture of methanol (150 ml) and concentrated hydrochloric acid (6.1 ml)
  6. customevaporated in vacuo
  7. customThe resulting residue was chromatographed on silica gel (250 g)
  8. washeluting with a mixture of chloroform and methanol (19:1, V/V)
  9. additionThe fractions containing the desired compound
  10. customwere collected
  11. customevaporated in vacuo

Sources & evidence

ORD record
ord-a9ac8d63a82d40849e086963aec1ff1e
Source dataset
uspto-grants-1990_05
Patent number
US04925838

Reaction notes

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